History Creator / OHenry

* BeleagueredChildhoodFriend: "After 20 Years."

---> "Around the first corner Stuffy turned, and stood for one minute. Then he seemed to puff out his rags as an owl puffs out his feathers, and fell to the sidewalk like a sunstricken horse."

* ConMan: Jeff Peters and Andy Tucker, protagonists in a cycle of stories, most notably "The Gentle Grafter."

--> Me and Pick ain't Wall Streeters like you know 'em. We never allowed to swindle sick old women and working girls and take nickels off of kids. In the lines of graft we've worked we took money from the people the Lord made to be buncoed--sports and rounders and smart Alecks and street crowds, that always have a few dollars to throw away, and farmers that wouldn't ever be happy if the grafters didn't come around and play with 'em when they sold their crops. We never cared to fish for the kind of suckers that bite here. No, sir. We got too much respect for the profession and for ourselves.

* IneffectualSympatheticVillain: "The Ransom of Red Chief."
* TheIrishMob / OfficerOHara: As many of the stories are set in New York in the late 19th/early 20th century, there are plenty of examples of both. ''The Coming-Out of Maggie'', for instance, involves an Irish-American gang and their girlfriends going to a dance. [[spoiler:The titular Maggie's date, Terry O'Sullivan, turns out to be an Italian mobster called Tony, who she pretends is Irish as she's sick of never having a date for the dances. Unfortunately, his cover is blown when the gang leader's captain in the police force has no idea who 'Terry' is.]]
* LetOffByTheDetective: ''A Retrieved Reformation''.

* PityTheKidnapper: TropeCodifier. In "The Ransom of Red Chief," two small-time criminals kidnap a BrattyHalfPint who proves to be so insufferable that the kidnappers end up paying a ransom to his father to take him back.

* TwistEnding
* VillainProtagonist: Because O. Henry spent time in jail, many of his stories, like "The Ransom of Red Chief." focus on (relatively) petty criminals.

* AmbiguouslyGay: It's implied about as strongly as possible for a 1907 story that Sue and Johnsy are lesbian lovers. They are artists in Greenwich Village (even then a {{Gayborhood}}), they have affectionate nicknames for each other (and Joanna has the masculine nickname of "Johnsy"), they call each other "darling", and Sue snorts with derision when the doctor suggests that a man might be the cause of Johnsy's despair.

* BalloonBelly: Poor [[LazyBum Stuffy Pete]] in "Two Thanksgiving Day Gentlemen", after [[spoiler:he guilt-trips himself into eating two huge Thanksgiving dinners in immediate succession provided by mutually unaware benefactors]]:

* BeleagueredChildhoodFriend: ''After 20 Years''.

* BrattyHalfPint: Johnny Dorset from ''The Ransom of Red Chief''.
* CantGetInTroubleForNuthin: ''The Cop and the Anthem''.
* ConMan: Jeff Peters and Andy Tucker, protagonists in a cycle of stories.

* CorruptCorporateExecutive: An early example in "Shark" Dodson from ''The Roads We Take''.
* DomesticAbuse: ''A Harlem Tragedy'', which, despite the title and the subject matter, is a very light-hearted story.
* DownerEnding: Occasionally, for example in ''The Furnished Room'' and ''The Last of the Troubadours''.
* DrivenToSuicide: A particularly dark example of this in [[spoiler:''The Furnished Room''. The woman the protagonist was looking for killed herself in said room - a fact the landlady covered up - and he also gasses himself to death.]]
* EvenEvilHasStandards: ''The Tempered Wind''. Two conmen, Parleyvoo Pickens (the narrator) and Buckingham Skinner, team up with a third conman and set up a business in New York selling fake bonds. However, a newspaper report exposes the business as fake, and the conmen get a nasty surprise when their customers show up at the office and are revealed to be poor factory workers, disabled war veterans, old women, and even children. One woman tells them about how she had invested all her life savings and needs the money back for her dying child, while the factory girls are losing money for missing work, and one women is in tears because she was saving for her wedding. [[spoiler:Pickens and Skinner give all the money back.]] When the reporter who wrote the article interviews the conmen again, Skinner says:

** A lesser-known O. Henry short story, ''An Unfinished Story'', used this to create the author's trademark twist ending. On Judgment Day, the narrator sees a long line of men waiting to go to Hell. Then the reader hears a sad story about a shop girl who only earns $5 a week. The story goes into details about her budget, how she sometimes goes hungry without anyone noticing, etc. She's about to accept a date from a rich man who has a taste for shop girls (whether he's a Romeo pimp or just likes to have kept women is not specified), but changes her mind at the last moment. The narrator says her story won't end until a night when she's feeling a little hungrier. Meanwhile, an angel tells the narrator that the long line of men are store owners who only paid their shop girls $5 a week, and asks "Do you belong with them?" "Not on your immortality," the narrator replies indignantly, "I only burned an orphanage and robbed a church!"
* ExasperatedPerp: ''The Ransom of Red Chief''.

* GoldDigger: Nancy and Lou in ''The Trimmed Lamp''. Lou works in a laundry, while Nancy works in a high-end department store with rich customers, whose style and mannerisms she imitates. Both live in hope of bagging a rich man, especially Nancy, as she earns less than Lou (which Lou keeps rubbing in her face). [[spoiler:Lou ends up with a rich man - but her boyfriend Dan leaves her for Nancy.]]
* IllGirl: ''The Last Leaf''.
* IneffectualSympatheticVillain: ''The Ransom of Red Chief''.

* MockMillionaire: ''Transients In Arcadia''; ''The Policeman O'Roon''
* NiceJobBreakingItHero: ''The Last of the Troubadours''.

* PityTheKidnapper: TropeCodifier. In ''The Ransom of Red Chief'' two small-time criminals kidnap a BrattyHalfPint who proves to be so insufferable that the kidnappers end up paying a ransom to his father to take him back.

* ThatManIsDead: ''A Retrieved Reformation'', in a way.
* TitleDrop: In "The Roads We Take", the protagonist wonders if he'd have turned out a different man if he'd made a key choice differently, and his colleague says "I reckon you'd have ended up about the same... It ain't the roads we take; it's what's inside of us that makes us turn out the way we do." The end of the story bears him out.
* TomatoSurprise: ''After Twenty Years'' has the revelation that [[spoiler:the main character is an infamous criminal.]]

* VillainProtagonist: Because O. Henry spent time in jail, many of his stories, like ''The Ransom of Red Chief'', focus on (relatively) petty criminals.

* TheIrishMob / OfficerOHara: As many of the stories are set in New York in the late 19th/early 20th century, there are plenty of examples of both. ''The Coming-Out of Maggie'', for instance, involves an Irish-American gang and their girlfriends going to a dance. [[spoiler:The titular Maggie's date, Terry O'Sullivan, turns out to be an Italian mobster called Tony, who she pretends is Irish as she's sick of never having a date. Unfortunately, his cover is blown when a local Irish bigwig, who knows the O'Sullivans, has no idea who 'Terry' is, and he pulls out a stiletto.]]

** A lesser-known O. Henry short story used this to create the author's trademark twist ending. On Judgment Day, the narrator sees a long line of men waiting to go to Hell. Then the reader hears a sad story about a shop girl who only earns $5 a week. The story goes into details about her budget, how she sometimes goes hungry without anyone noticing, etc. She's about to accept a date from a rich man who has a taste for shop girls (whether he's a Romeo pimp or just likes to have kept women is not specified), but changes her mind at the last moment. The narrator says her story won't end until a night when she's feeling a little hungrier. Meanwhile, an angel tells the narrator that the long line of men are store owners who only paid their shop girls $5 a week, and asks "Do you belong with them?" "Not on your immortality," the narrator replies indignantly, "I only burned an orphanage and robbed a church!"

* EvenEvilHasStandards: ''The Tempered Wind'. Two conmen, Parleyvoo Pickens (the narrator) and Buckingham Skinner, team up with a third conman and set up a business in New York selling fake bonds. However, a newspaper report exposes the business as fake, and the conmen get a nasty surprise when their customers show up at the office and are revealed to be poor factory workers, disabled war veterans, old women, and even children. One woman tells them about how she had invested all her life savings and needs the money back for her dying child, while the factory girls are losing money for missing work, and one women is in tears because she was saving for her wedding. [[spoiler:Pickens and Skinner give all the money back.]] When the reporter who wrote the article interviews the conmen again, Skinner says:

William Sydney Porter (1862-1910), PenName O. Henry, is an American writer of chiefly short fiction (the most famous piece being "Literature/TheGiftOfTheMagi") and one novel (''Cabbages and Kings''). His stories are famous for their [[MandatoryTwistEnding Mandatory Twist Endings]], warm characterization and wit.

William Sydney Porter, PenName O. Henry, is an American writer of chiefly short fiction (the most famous piece being "Literature/TheGiftOfTheMagi") and one novel (''Cabbages and Kings''). His stories are famous for their [[MandatoryTwistEnding Mandatory Twist Endings]], warm characterization and wit.

* PityTheKidnapper: In ''The Ransom of Red Chief'' two small-time criminals kidnap a BrattyHalfPint who proves to be so insufferable that the kidnappers end up paying a ransom to his father to take him back.

* PityTheKidnapper: ''The Ransom of Red Chief''.

[[caption-width-right:278:As his mustache demonstrates, he liked twist endings.]]

* TrickTwist

* AllJustADream: ''The Roads We Take'', although it is more a case of IronicEcho.

* TrainJob: ''The Roads We Take''.

* BalloonBelly: Poor [[LazyBum Stuffy Pete]] in "Two Thanksgiving Day Gentlemen":

* DownerEnding: Occasionally, for example in ''The Furnished Room''.

For some inexplicable reason, he is [[GermansLoveDavidHasselhoff most popular in the former USSR republics]], where phrases such as "Bolivar cannot carry double" have become stock quotes.

[[caption-width-right:278:He liked twist endings in his stories and his mustache]]

* MockMillionaire: "Transients In Arcadia"; "The Policeman O'Roon"

* VillainProtagonist: Because O. Henry spent time in jail, many of his stories, like ''The Ransom of Red Chief'', focus on (relatively low-time) criminals.
* WildWest: Another popular setting. Is usually limited to Texas ranches.

* TomatoSurprise: "After Twenty Years" has the revelation that [[spoiler:the main guy is an infamous criminal.]]